


Imagine: Finding out why Dean left you

by PsychedelicBoomerang



Category: Supernatural
Genre: Alcohol, Angst, Drunk Reader, F/M, Flirting, Old Relationships, a little plot, relationships
Language: English
Status: Completed
Published: 2020-11-17
Updated: 2020-11-17
Packaged: 2021-03-10 00:35:30
Rating: Teen And Up Audiences
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 1,003
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/27604996
Author URL: https://archiveofourown.org/users/PsychedelicBoomerang/pseuds/PsychedelicBoomerang
Summary: Your an old flame of Dean's from high school - you make amends and things get a little flirty. Until you ask why he left you at a party you were both attending.
Relationships: Dean Winchester / Female Reader, Dean Winchester / OC, Dean Winchester / Reader, Dean Winchester / Reader Insert, dean winchester / you
Kudos: 7





	Imagine: Finding out why Dean left you

“So – W-why _don’t_ you like my sister?” You slurred over your words as you leant up against Dean, grinning playfully up at him as he rolled his eyes. It wasn’t the first time tonight that you had asked and he knew it wasn’t going to be the last. You hadn't seen him since you were teenagers until a few nights ago when you spotted him in your local bar. He hadn't changed a bit and it was almost like the years had never passed, you were still crushing hard on him.

  
“I told you, I don’t want to talk about it.” He spoke flatly before drinking from his beer, smiling softly at you as his eyes studied you. “Besides, its petty. Its not interesting and you’re drunk.”

  
“I am _not_ drunk. A li-little bit tipsy. And I like petty,” you fluttered your eyelashes at him as you sat up straight, trying your best to appear sober. You watched a half hearted smile grow across his face as you rested on his shoulder again. "Petty can be interesting."

  
“I’m telling you, its nothing important. Now, drop it.” His voice was firm but you could see he didn’t mean to snap. You sat up straight, this time looking closely at him. He obviously didn't want to tell you, but you couldn't let it go now. Something was wrong.

  
“You can tell me. Why don’t you like her?” You persist, smiling sweetly at him. “I promise I won’t tell her.”

He remained silent for few moments, thinking hard about what to say next. He knew you wasn't going to drop the subject - you were just as stubborn as ever and a smile tugged at his lips when he an image of you both in your younger days suddenly resurfaced. He couldn't not tell you. You had the right to know.

  
“Do you remember Molly Newman?” He spoke suddenly after drinking his beer again.

  
“Molly Newman? From that house party we went to? I remember her very well…” You could feel your senses coming back, the effect of the wine slowly fading. Her name alone made you seethe; she was always so pretty and delicate to do anything herself. She loved the boys cooing over her and she thrived on the attention they gave her. “What about her?”

  
He shuffled uncomfortably on his seat, looking down at the beer bottle in front of him as he thought carefully about what to say next.

  
“Well, your sister said that..uhm, she said you were going to leave me for good.” He sighed heavily, sitting back as he folded his arms across his chest. Anger slowly filled the pit of your stomach, realisation hitting you quickly. “She said that you were seeing someone else and that it was serious with you and this mystery man."

  
“Wait, my sister said that?” You question him, feeling your heart begin to sink. “Why – Why would she–?"

  
“That’s what she told me. So, being drunk and angry, I kissed Molly Newman.” He cut you off quickly, looking away from you, his cheeks burning a crimson red. You couldn't tell if he was angry at himself for believing you sister all those years ago, or angry at you and believing it to have been true.

  
“Dean, was that while we were together?” You were both sat in silence for what felt like hours before he finally looked up at you, his eyes heavy with guilt. “Is that why you left me at the party?”

  
The memories of the last time you saw him came flooding back, tears threatening to fall down your cheeks. You were told he was last seen in the carpark of the apartment building you were both at, helping a girl in to her car. It never once occurred to you that it would have been someone he intended on going to bed with. You thought so much more of him than to be unfaithful.

  
“She said you were going to leave me. That I wasn’t good enough and that you were already with someone,” He sighed heavily, his eyes meeting with yours. "Someone who could look after you, someone your father approved of."

  
“Dean, there was never anyone else…” Your breath caught in your throat as you wiped away your tears. "And my dad thought the world of you, you know both my parents did. Do you really think I would have done that to you?”

  
“Oh God, no… I don’t know. At the time I did, I guess. At the time I didn’t know what to think.” He held his face in his hands before sitting up quickly to look back at you. "It messed me up, she told me to get out of town. To forget about you. I thought you were over me and with someone else--"

  
“I was only ever with you Dean. It was always you Dean,” Your voice broke, tears falling freely as you tried to keep your composure. “A thousand times over it would have been you.”

  
“Y/N, baby, you’re drunk… it was a long time ago.” He looked back down at his drink, avoiding your gaze. Anger flooded you for a moment, sobering you up faster than a glass of water ever would have. You were angry at your sister for getting involved and for a split second, you were angry at Dean for ever thinking that of you. “You deserved so much better.”

  
“I’m not drunk. I would have picked you every time. _Every_ single time. I still would…” Suddenly his hand found yours from across the table, his eyes locking with yours as his jaw clenched tightly. 

  
“And I would pick you.” His voice was a soft whisper as he squeezed your hand, helplessness washing over him.

“She – she bro—”

  
“Y/N, don’t say it. It was a long time ago. Please, don’t say it.” He was pleading with you, the realisation of the past dug up and hitting him.

  
“She broke us up. She made us break up…”


End file.
